Over the past 18 months, I have performed 5 successful SBS2011 to Server 2016 Essentials with on-premises Exchange 2016 for clients of mine, thanks to excellent migration guidance and support from Server-Essentials. All has been well for months, with clients using various versions of Outlook, ie 2010, 2013, and 2016, and a couple of users with the Office 365 version
I now have several users, using Outlook 2016, on computers both attached to the domain or visiting, or connecting from other locations, where the autoconnect does not work.
Some research on the problem reveals a lot of frustrated attempts to deal with it, and that is has been experienced for some time in various circumstances. When completing the migrations, we had no such trouble - it has only begun recently, but on 3 separate systems.
Connection of earlier Outlook versions than 2013, and mobile device Outlook apps, and OWA, all continue to work correctly. OWA provides a workaround, at least.
The failure to connect only produces a 'something went wrong' message. I have had a protracted 'support' session with Microsoft, which revealed a number of registry keys, and then failed to continue - typically there were hour-long waits for any response, and when I opened Outlook the next time, the promised continuation of the diagnosis did not reconnect.
My clients have not considered moving to Office 365, since they own licensed versions of Office and Exchange, and one of them has a substantial contacts database which is integrated with Exchange via a SQL database.
I post this to ask for advice - if I were to add Exchange 365 Integration to these systems, would this allow accounts established on the on-premises Exchange to continue to work as before, simply by not migrating those accounts? Or is there anything we can do to resolve the connection problem with the current Outlook clients?
Hoping for some inspiration to replace my frustration!